I was back at the bar, drinking alone, assessing alternative options of which there were few. Hoping to see Dana again. Hoping lightning might strike twice. Debating between approaching a middle aged blonde sure thing that looked somewhat like a bitchy teacher I once hated, or a pretty college thing that couldn’t have been a day over nineteen and had the full attention of every guy in the bar.
And then Dana appeared, looking as fuckable as always in a little black dress that straddled the line between casual and trashy, emphasizing her petite frame, accentuating her hips and doing miracles to her small breasts. Just enough makeup. Hair tied back. Lipstick and a pout. A bit of a sparkle on her olive skin.
She wasn’t alone.
‘This is Jack. He’s got some coke and a room in the hotel upstairs, don’t you jack?’
Jack nodded. Jack was about ten years older than her, than us. Jack looked like a well-to-do date rapist, well built, a ring on his finger and a cunty smirk on his chiselled face. I fucking hated Jack.
‘Jack says he’s hung. We’re going to go upstairs and fuck, aren’t we Jack?’ He nodded and grinned. ‘Come with us. You can watch. I like being watched. Wanna watch Jack fuck my brains out?’
Filthy Dana. I couldn’t believe the words I was hearing, but I found myself nodding. Hot trumps weird. I wasn’t turning down a free show.
Ten minutes later we were in Jack’s hotel room. It was plush but small – a large bed, a small couch a little balcony and not much else. I sat beside Dana on the couch, Jack sat on the bed and we did some large lines of mediocre coke off the small coffee table while sipping on overpriced, underwhelming beer.
After the second or third line Dana was wired, wide eyed and grinning. She excused herself to pee, leaving Jack and I sitting there in the most awkward of silences.
She took an agonizingly long time, and when she finally emerged she was wearing nothing but a strapless bra, holding her panties up on display. ‘They’re soaking.’ She said, tossing them at me with a giggle as I stared. They were, indeed, soaking. There’s no way to sniff panties and not look creepy, but I did it anyway.
Jack leapt off the bed and walked over to her, towering over her. They kissed, which seemed quite awkward given that there was over a foot of height difference between them.
Dana sat on the bed and I considered looking away but just kept on staring, as Jack peeled off his shirt and she worked on his belt. As she pulled his jeans down she froze.
‘OH. MY. GOD’ she stammered in amazement. Jack was hung. It was hard not to stare. ‘It’s not even hard yet…’ she muttered in disbelief. Limp, he was bigger than me erect. Dana tugged it and I finally started to feel awkward enough to divert my gaze for a while. I read the label on the bottle of beer and glanced out the window and when I looked back Jack was wrapping up. Hard, it looked like a fucking weapon. Not much longer but significantly thicker. I was jealous of Jack for more reasons than one.
Dana wrapped her lips around it and I couldn’t look away. In her little, gaping mouth it looked terrifying. She spat it out and gasped. ‘It’s too big’.
I looked away again, suddenly aware that I was rock hard and oozing. Weirdly disconcerted by how much I was enjoying the show. I helped myself to a line and when I looked back up Jack was mounting her and she was looking right at me.
‘OH FUUUCKKKKK’ Dana wailed as Jack entered her, her eyes bulging. ‘fuck fuck fuck fuck fuck’ she gasped as Jack pushed in. ‘oh my god oh my god…’ she gasped as Jack withdrew. Jack started thrusting and she made noises like a wounded animal. Yelps and squeals and grunts and howls.
‘Stop’ she begged and Jack obeyed. ‘Let me ride it’. Music to my ears. A different view. I looked away as Jack pulled out and when I looked back up Dana was kneeling on top of him, her back to me, holding his behemoth in her little hand. I stared unashamedly.
I watched her guide his tip between her dangling lips. ‘Oh fuck Jack it’s so big’ she whimpered as she slowly lowered herself, as it crept in, as I inadvertently rubbed myself through my jeans while I watched it happen. ‘It’s so fucking big’
There were no eyes judging me. I shifted sideways so I was perfectly behind them, so I could see every detail. Her perky ass jiggled as she wriggled, slowly taking his thick, sheathed cock deeper, her swollen lips clinging as it stretched her apart. ‘Don’t move Jack… let me do it… oh fuck Jack…’
It was hard not to notice that Jack shaved his balls. Dana leaned forward and started to slowly ride him. Jack grabbed her ass with his big hands and gifted me a view of her puckered asshole. Things started to get creamy. She gasped his name over and over and over again.
I was stupidly hard. Watching was fun, once I managed to shrug away the weird. No pressure. No expectations. No idea what to do with my throbbing, oozing erection.
I knew what I wanted to do. Whip it out, climb on the bed and shove it up her ass. Obviously. I’ve seen porn. If only I had the confidence. Confidence was all I needed. I helped myself to another line. For confidence.
Just do it, I told myself. I started to fiddle with my belt. Maybe I should ask first? How would I ask? Excuse me, would you mind if I sodomized you for a bit? Room for one more?
Just do it, I told myself. See what happens. As I started to unzip Jack pressed a creamy finger into her little ring and I silently cursed him. ‘OH JACK… don’t stop… please Jack..’
Fuck Jack. Now what was I supposed to do? Excuse me, would you mind dislodging your finger Jack? Fuck Jack. I watched it creep deeper, enjoying the view but getting frustrated. And jealous. And somehow, harder. Dana was getting creamier.
‘JAAACKKK!’ she shrieked as she came. She arched her back and for the first time she took his whole length inside her. I watched her cheeks tighten and her thighs tremble as she squealed a never ending squeal. ‘oh Jack…’ she gasped, going limp.
Jack pulled his finger out and I jumped to my feet. Hesitation wasn’t fucking me again. Just do it. Do it like they do in porn. I reached into my jeans and as soon as I managed to pull my sticky erection free Jack rolled over so he was on top of her.
FUCK JACK.
I was standing there with my cock in my hand staring at Jack’s thrusting ass. I tucked it the fuck away as quickly as I’d whipped it out, quickly moving over to the mini bar to get another beer and a view of anything other than ass.
There was nothing to see but Dana’s arms and legs and a whole lot of Jack. Thrusting, making the bed creak as Dana whimpered from beneath him. Jack was grunting. Thrusting harder, making Dana Yelp as the bedposts knocked against the wall.
I just stood there and watched as he pulled out, as he tore the condom off, as he lurched forward and exploded all over her chest and neck.
‘Filthy little whore’ he groaned, stroking himself, emptying his dregs on her.
‘Do you kiss your wife with that mouth?’ Dana replied.
‘Fuck you. Don’t talk about my wife.’ Jack snapped back. Triggered. He climbed off her, off the bed and I just kept staring at Dana, at her glistening skin and the mess Jack made. He walked into the bathroom, tossed her dress through the doorway and slammed the door. I walked around to the foot of the bed and stared unashamedly between her splayed legs, at her mangled, swollen, creamy, gaping vagina.
‘We should probably leave’ she said, starting to sit up. I grabbed her feet and pulled her toward me, to the edge of the bed, back on her back. ‘I’m in no for state to flee’ I replied, unzipping, pulling my desperate erection free.
‘I take it you enjoyed the show’ Dana giggled.
‘It had its moments’ I grunted, shoving myself unceremoniously into her cavernous void.
‘Do you think I’m a filthy little whore?’ she asked, looking up at me, covered in cum, a large, used condom draped over her shoulder as I used her. ‘In general or at this precise moment?’ I teased.
‘Fuck you. Hurry up. We really should get out of here.’
I came inside her. Sweet, undignified relief. Five, maybe six thrusts. She barely waited for me to finish before she pushed me away, peeled the rubber off her shoulder and used the blanket to mop up Derek’s mess.
Her dress was on before I’d even zipped up. I was still oozing into my shorts as we fled the scene. We trotted down the hallway into the elevator, and as soon as the doors closed Dana laughed.
‘I took his coke. Please, please tell me you have my panties?’
I reached into my pocket and pulled them out. ‘You creepy fucker. Thank you. I’m leaking’ She said, snatching them off me.
I thought she’d put them on but instead she did a half squat, reached under her dress and did something else. It took me a second to realize she was stuffing them inside her.
‘You might not be a whore but you most definitely are dirty’ I joked.
‘I can accept that’ she giggled.
As we made our way through the lobby I noticed she was walking funny, almost hobbling.
‘I think Jack ruined me’ she said, reading my mind.
Ten minutes later we were in another hotel bar, having a much needed drink. Dana kept shifting in her seat and all I could do was think about the panties she had inside her.
We talked about what had just happened, a filthy post-fuck analysis that I truly enjoyed. Jack was the biggest she’d ever had. It hurt, but she enjoyed it. She didn’t mind his mess but hated being called a whore, ‘the way he said it’. She liked being watched. She liked that I liked watching, but was surprised that I didn’t ‘get involved’.
‘I loved it when you used me. That was so fucking dirty. Just dumping your cum inside me while that fucker was in the bathroom. God that was hot..’
I almost told her I loved her.
‘I don’t know about you but I’m ready for another round’ she said. I agreed and she walked off to the bar. I would’ve done it myself, but our chat had made me a bit hard.
Five minutes later she returned, without drinks but with a guy who looked like a surfer in a suit. ‘Another round’ I muttered to myself, the penny finally dropping.
‘This is… Jacob?’ she said. Jacob nodded and politely reached out his hand. Jacob was tall and lithe and looked like he sold gym equipment or some shit. Younger than Jack, and significantly better looking than me. Like Jack, Jacob was married. Like Jack, Jacob also had a room in the hotel upstairs.
‘Ready?’ She asked with a cheeky smile.
Filthy little whore.
Source: reddit.com/r/gonewildstories/comments/mobypj/watching_dana_fuck_mf
Fuck Jack.